- Must visit
Art Institute Of Chicago
One of the premier art museums in the US, known for Impressionist masterpieces, modern works, and the iconic bronze lions at its entrance.
Cheapest price
$306
Average price
$422
Fastest journey
20 h 35 m
Average duration
21 h 5 m
Trains per day
2
Distance
901 km
The best way to find a cheap train ticket from Culpeper, VA to Chicago, IL is to book your journey as far in advance as possible and to avoid traveling at rush hour.
The average ticket from Culpeper, VA to Chicago, IL will cost around $422 if you buy it on the day, but the cheapest tickets can be found for only $306.
Of the 2 trains that leave Culpeper, VA for Chicago, IL on Sun, Jun 21, 1 travel direct so it’s quite easy to avoid journeys where you’ll have to change along the way.
On Sun, Jun 21 the direct trains cover the 901 km distance in an average of 21 h 5 m but if you time it right, some trains will get you there in just 20 h 35 m .
On Sun, Jun 21 the slowest trains will take 21 h 35 m and usually involve a change or two along the way, but you might be able to save a few pennies if you’re on a budget.




Omio recommends booking the train as it is the most popular option from Culpeper, VA to Chicago, IL among Omio's users. If you are prioritising price take the train with prices starting from $154. For those with little time consider booking a flight which can get you there in 5h 28m. The ticket price range depends on the travel mode: a train costs an average of $154, and a flight costs an average of $278.
Distance: 559 miles (901 km)
Most popular Train | Flight | Driving |
|---|---|---|
$222 Average price Cheapest | $351 Average price | $138 Average price (fuel + tolls) |
20h 6m Average total duration 19h 36m Onboard + 30m Additional time* | 8h 28m Average total duration Fastest 5h 28m Onboard + 3h 0m Additional time* | 11h 10m Average total duration (door-to-door) |
Direct Options | Direct Options | Direct Options |
This is compared to other travel options from Culpeper, VA to Chicago, IL:
A train is $130 (€106) less than a flight for this route with tickets for a flight from Culpeper, VA to Chicago, IL costing on average $351 (€288).
Other travel options to Chicago, IL take longer:
Train takes on average 19h 36m.
Tickets start at around $222 (€182) compared to roughly $138 (€113) in fuel and tolls — a saving of about $-84.43 (€-69.08). The journey takes 19h 36m versus 11h 10m by car, so you'll arrive a bit later, but you can work, read, or sleep along the way rather than spending the time behind the wheel. You'll also save the hassle of parking at the other end.
Driving is worth it if you're on a tight schedule, travelling as a group, or want to stop somewhere en route.
The table below shows live departures for Culpeper, VA to Chicago, IL trains for today, Saturday, June 20. You can also manually refresh the results below to see updated train journeys.
| Provider | Departs | Duration | Arrives | Transfers | Tickets |
|---|---|---|---|---|---|
20 Crescent · 40 Floridian | 11:51 AM Culpeper Station, Culpeper, VA | 21h54 | 8:45 AM Chicago Union Station, Chicago, IL | 1 transfer | |
156 Northeast Regional · 40 Floridian | 12:10 PM Culpeper Station, Culpeper, VA | 21h35 | 8:45 AM Chicago Union Station, Chicago, IL | 1 transfer | |
| Sunday, June 21 | |||||
![]() | 12:10 PM Culpeper, VA | 20h35 | 8:45 AM Chicago, IL | 1 transfer | |
![]() | 12:25 PM Culpeper, VA | 21h35 | 10:00 AM Chicago, IL | 0 transfersDirect | |
This is the last train of the day. | |||||
Find all the dates and times for this journey
Compare train and flight prices over the next three weeks. See the best deals at a glance, find the lowest fares, and choose the option that fits your budget.
Trains from Culpeper, VA to Chicago, IL run on average 2 times per day, taking around 19h 36m. Cheap train tickets for this journey start at $154 (€126) if you book in advance.
There are 1 trains per day. The earliest train runs at 17:55, the last at 18:40. The fastest train covers the 559 miles (901 km) distance in 21h 54m.
Distance 559 miles (901 km) |
Average train duration 19h 36m |
Cheapest ticket price $154 (€126) |
Trains per day 2 |
Direct trains 1 |
Fastest train 21h 54m |
First train 5:55 PM |
Last train 6:40 PM |
Cheapest Month Feb |
Cheapest Day Fri |
High Season Jan - Mar |
Low Season Apr - Jun |
Discover the best of Chicago — top attractions, local food, transport tips, budget advice, and currency essentials. Plan your perfect Chicago trip today.
One of the premier art museums in the US, known for Impressionist masterpieces, modern works, and the iconic bronze lions at its entrance.
Major natural history museum famous for Sue the T. rex, ancient cultures, and extensive science collections that appeal to both adults and children.
Large hands-on science museum in Hyde Park featuring a submarine, space exhibits, engineering displays, and immersive family-friendly experiences.
The city’s signature public space, home to Cloud Gate, gardens, events, and major skyline views that define modern Chicago.
Famous stretch of Michigan Avenue lined with historic buildings, shops, hotels, and frequent first-time visitor photo stops.
Highly popular waterfront promenade with architecture views, bridges, and one of the best urban walks in the city.
Chicago’s iconic thick-crust pizza baked in a deep pan, layered with cheese, toppings, and chunky tomato sauce. It is one of the city’s most famous comfort foods.
An all-beef hot dog on a poppy seed bun topped with mustard, onions, neon relish, tomato, pickle spear, sport peppers, and celery salt. It is a classic local street food.
Thinly sliced roast beef piled onto an Italian roll, often dipped in seasoned jus and topped with sweet peppers or giardiniera. It is a defining Chicago sandwich.
A historic old-school steakhouse serving steaks, chops, and classic Italian-American dishes in a traditional setting.
Chicago’s internationally acclaimed fine-dining restaurant known for highly inventive tasting menus and exceptional service.
A long-established Chicago favorite known for buttery deep-dish pizza and a casual, family-friendly atmosphere.
Moderate for a major U.S. city: casual food is manageable, but hotels, attractions, and downtown dining can be pricey.
Tip 18-20% in restaurants; 20%+ for great service. Tip bartenders USD 1-2 per drink, taxis about 10-15%, and hotel staff a few dollars.
Find answers to the most common questions about traveling from Culpeper, VA to Chicago, IL by train. From journey times and ticket prices to direct connections, first and last departures, and even whether the route is scenic, our FAQs cover everything you need to plan your trip. Whether you’re looking for the fastest train, the cheapest option, or tips for making the most of your visit at Chicago, IL, this guide helps you travel smarter and with confidence.

Most Culpeper, VA to Chicago, IL trains use the Culpeper Station to Union Station station pair. Use this guide to compare Culpeper, VA and Chicago, IL train stations on this route, check city-centre transport, alongside checking practicalities like train station facilities and services.
Culpeper Station has practical services for this route, including Parking, Dining, Taxis, Accessibility, WC, Hotel, Ticket Office, and Information Desk.
Food options include: KFC, Deli Cious, Dee Dee's Family Restaurant
Ticket office support is available at Culpeper Station. Information desks are located in the main hall.
Available at Culpeper Station: Parking, Taxis, WC.
Accessibility facilities are available at Culpeper Station: Ramps.
Nearby hotels include Holiday Inn Express & Suites Culpeper, Best Western Culpeper Inn, Microtel Inn & Suites by Wyndham Culpeper.
Union Station is 3 km from Chicago city centre. Public transport options include:
Union Station has practical services for this route, including Wifi, Lockers, Parking, Dining, ATM, Taxis, Accessibility, WC, Hotel, Lounge, Lost and Found Office, Ticket Office, Bike Parking, Car Rental, Information Desk, and Luggage Carts.
Food options include: The Chicago Firehouse Restaurant, Lou Mitchell's
Free. ATMs are available in the train station.
Ticket office support is available at Union Station. Information desks are located in the main hall.
Luggage storage is available at Union Station. Lost and found is available at the station.
Available at Union Station: Parking, Taxis, WC.
Available at Union Station: Bike Parking, Car Rental.
Accessibility facilities are available at Union Station: Elevators, ramps, restrooms.
Nearby hotels include The Kimpton Gray Hotel, JW Marriott Chicago, W Chicago - City Center.
Here are some other resources that might have the information you need